Boron tribromide → 2,6-Dichloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoic acid

HRID 1058396Notes

Reaction equation

HRID 1058396 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=2)=[O:13])[CH:9]=[C:8]([Cl:24])[C:3]=1[C:4]([O:6]C)=[O:5].C(=O)=O.CC(C)=O.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[O:13])[CH:9]=[C:8]([Cl:24])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 18522661Acetone cardiceHCID 865863302,6-Dichloro-4-[[(3-methoxybenzyl)amino]carbonyl]benzoic acid, methyl ester

Product 1

HCID 226615502,6-Dichloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 2,6-dichloro-4-[[(3-methoxybenzyl)amino]carbonyl]benzoic acid, methyl ester (11.83 g, 32.1 mmol) in dichloromethane (400 mL) was cooled to ˜−78° C. (dry ice-acetone bath) and boron tribromide (1M in dichloromethane; 100 mL, 100 mmol) was added. The mixture was stirred in the cooling bath for 3 h and then allowed to stand at room temperature for 72 h. The supernatant was decanted off and water (300 mL) was added to each of the supernatant and the residue. The mixtures were stirred at ˜40° C. for 1 h and then the solids were collected by filtration, combined and air-dried to give 2,6-dichloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoic acid (8.73 g, 80% yield) as a cream-colored solid.

Workup

  1. additionwas added
  2. waitto stand at room temperature for 72 h
  3. customThe supernatant was decanted off
  4. additionwater (300 mL) was added to each of the supernatant
  5. stirringThe mixtures were stirred at ˜40° C. for 1 h
  6. filtrationthe solids were collected by filtration
  7. customair-dried

Sources & evidence

ORD record
ord-69199ab7b3f84964a33f6afb9390f138
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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